Triethylamine → HCID 57033160, compound

HRID 566997Notes

Reaction equation

HRID 566997 reaction equation
[CH2:1]([O:4][N:5]1[C:14](=[O:15])[C:13]2[C:16]([Cl:20])=[CH:17][C:18](Cl)=[C:11]3[C:12]=2[C:7](=[CH:8][CH:9]=[C:10]3[Cl:21])[C:6]1=[O:22])[CH:2]=[CH2:3].[C:23]([O:27][C:28](=[O:35])[NH:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)([CH3:26])([CH3:25])[CH3:24].C(N(CC)CC)C>C(#N)C>[C:23]([O:27][C:28](=[O:35])[NH:29][C@H:30]1[CH2:34][CH2:33][N:32]([C:18]2[CH:17]=[C:16]([Cl:20])[C:13]3[C:14](=[O:15])[N:5]([O:4][CH2:1][CH:2]=[CH2:3])[C:6](=[O:22])[C:7]4[C:12]=3[C:11]=2[C:10]([Cl:21])=[CH:9][CH:8]=4)[CH2:31]1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 22623918HCID 22623918, compound

Product 1

HCID 57033160HCID 57033160, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-allyloxy-4,6,7-trichlorobenzo[de]isoquinoline-1,3-dione (0.44 g, 1.2 mmol, from Example I4), (S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester (0.3 g, 1.5 mmol), triethylamine (0.2 g, 2.0 mmol), and 20 mL of acetonitrile was stirred at room temperature for 6 hours. The solvent was removed in vacuo and the residue partitioned between water and dichloromethane. The organic layer was dried and evaporated in vacuo. The residue was chromatographed on silica gel (ICN 230-400 mesh) eluting with dichloromethane/ethyl acetate (80:20) to give 0.35 g of the title compound, mp 123-125° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water and dichloromethane
  3. customThe organic layer was dried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel (ICN 230-400 mesh)
  6. washeluting with dichloromethane/ethyl acetate (80:20)

Sources & evidence

ORD record
ord-691612272d8849e0a25d4bf919baa11e
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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